chemistry

General Organic Chemistry

Sakshi Vora

IIT - Roorkee

10th, 12th CBSE State Topper

7+ Years of Teaching Experience

KVPY fellow
Telegram Channel
 Unacademy
Subscription

LIVE Class Environment Performance Analysis

LIVE Polls & Leaderboard Weekly Test Series
LIVE Doubt Solving DPPs & Quizzes
LIVE Interaction
 India’s BEST Educators Unacademy Subscription

If you want to be the BEST

“Learn” from the BEST
Bratin Mondal Top Amaiya singhal
100 %ile 100 %ile
Results
 11th / 9, 10

12th / Drop

SAKSHI SAKSHI
General Organic Chemistry
Types of Bond Fission
Homolytic Bond Fission
Bonding e- are equally distributed between bonding atoms so that
electrically neutral intermediate radicals are obtained.

Note - Any bond can be cleaved by homolytic pattern. It never

depends upon the type of atom. (no condition of eneg of A & B)
Heterolytic Bond Fission

In such kind of bond breaking, bonding electrons transfer towards

more electronegative atoms so that ions are obtained

Condition: Electronegativity of A and B should be different

Note :

1. Heterolytic bond fission usually takes place in polar solvents.

2. Homolytic bond fission generally take place in any solvent.
3. Free radicals are generally obtained in non - polar / gaseous
phase.
Practise Questions
Break the molecules in the given conditions

Water, heat

heat
Break the molecules in the given conditions

Water, heat

sunlight
Reaction Intermediates
 Carbocation

➔ Trivalent
➔ Incomplete octet
➔ Highly unstable
➔ Highly reactive
➔ Only six e
➔ Lewis acid (Which have tendency to gain e’s)
➔ BP (Bond Pair) = 3
➔ UP (Unpaired electrons) = 0
➔ Diamagnetic
 Carbocation

Lone pair = 0
Magnetic moment = 0
Hybridization : sp2
Bond angle = 120o
Trigonal Planar
Vacant orbitals available
Carbon Free Radical
> Trivalent
> Incomplete octet
> Highly unstable
> Reactive
> Can’t act as lewis acid
> Paramagnetic
> BP =3
> UP = 1
> LP = 0
> MM = √3 BM
 Carboanion

> Complete octet

> Highly unstable
> Reactive
> BP = 3
> LP = 1
> MM = 0
> Pyramidal
> sp3
> Bond angle ≤ 108o
> Diamagnetic
Practise Questions
 Match The
column

Column 1 Column 2

A. Carbocation CH3 P. Paramagnetic

B. Carbanion CH3 Q. Diamagnetic

C. Carbon free radical CH3 R. Electron deficient central

atom

D. Ammonia NH3 S. Sp2 hybridisation

T. Sp3 hybridisation
Electron Displacement Effect
 Electronic Displacement Effect
Effect caused due to the displacement of e-s

Electronic Displacement Effect

Permanent Effect Temporary Effect

(this effect appears only

in the presence of
Inductive Resonance Hyper conjugation external cause)
OR
Mesomeric
Inductomeric Electromeric
effect effect
Inductive Effect
Inductive Effect
Permanent displacement of σ e- in any covalent bond due to
difference in ENeg of attached otom/group with C
 Inductive Effect

> Permanent effect

> Due to electronegativity difference
> Reference is C-H
> Distance Dependent
> Operates only on sigma electrons
> Weak effect
Types of Inductive Effect
 -I effect

Order of rate of withdrawing σ e-

-NF3+ > -NR3+ > -NH3+ > -NO2

> -CN > -COOH > -F > -Cl > -Br > -I

> COOR > -OR > - OH > -NH2 > -C ≡ CH

> -Ph > -CH = CH2

 +I effect

+I series

-CH2- > -NH2- > -O- > -COO- > - C

CH3

> - CH > - CH2 - CH3

CH3

> - CH3 - T > D > H

Practise Questions
What is the correct order of +I effect of the following groups.

A. a > b > c > d > f > e >g

B. a > c > d > b > e > f > g
C. a > c > b > d > f > e > g
D. a > f > b > d > e > c > g
Resonance
Resonance

It is the permanent displacement of pi e density due to P/d orbital of

directly attached atom/group effect.
Resonance

Various structures required are known as resonating structures/ contributing

structures/ canonical structures.
Resonance

> Resonating structure which contributes the most in resonance

hybrid is known as its most contributing structure.

> Each resonating structure contributes in proportion of its

stability.
Conditions for Resonance
 Conditions for Resonance

(i) Compound must be planar (sp/sp2)

(ii) Compound must be conjugated.
(at least 3 p orbitals which are adjacent and parallel.
Important Examples
Compounds showing Resonance

+
Compounds showing Resonance

+ -
Important Point
Important Note:

If p electrons are present adjacent to any lone pair atom, then the
atom must be sp2 hybridized and one of its lone pair must be present
in a pure p orbital
Calculation of number of pi electrons

Number of pi electrons = number of electrons in pure p orbitals

Rules for drawing Resonating structures
Rules for drawing Resonating Structure

Rule - 1
Each RS of a compound must have a valid structure (octet rule
must be followed except atoms with variable valency)
Rules for drawing Resonating Structure

Rule - 2
Each RS must have same number of unpaired electrons
Rule - 3
Each RS must have each atom at its own position and must be
same in all RS. Resonance is a phenomena of delocalization of π-
electrons only (no movement of σ electrons)
Rule - 4
RS having unlike charges on adjacent same atoms is usually
neglected in consideration to contribution to hybrid as they are
highly unstable.
Calculation of total number of
Resonating Structures
Calculation of total number of RS
Calculation of total number of RS
Calculation of total number of RS
Calculation of total number of RS
Calculation of total number of RS
Drawing Resonating structure
Substituting Benzene
+R and -R Effect
Group showing +R Effect

-F - Cl , - Br -I -

OH -OR NH2

-NHR -NR2 - O- -NHR - CH-2 -

NHCOCH3
 Groups showing -R effect

-A = B - A ☰ B (EB > EA)

O
+ O O
-CH2 -BH2 -C ll ll
H -C- -N

O O
O O ll ll
-C -C -C - S - OH -C≡N
H OR
ll
NH2 O
Rules for stability of Resonating
Structures
Rule - 1

Resonating structure having complete octet is relatively more stable

+
CH2 F
+
N O
+
CH3 C O
Rule - 2
Resonating structures having higher no. of covalent bonds or is
neutral, is relatively more stable
Rule - 3
Resonating structures having -ve charge on the more
electronegative & +ve charge on the more electropositive atom is
relatively more stable
Rule - 4
Resonating structures having unlike charges closer and like
charges away are more stable

Me + Me Me + Me
N N

-
Rule - 5
Resonating structures having higher no. of benzenoid segments is
relatively more stable.

Benzene

I II

I = II
Stability
 Types of Conjugation

Extended Conjugation Cross Conjugation

Must have 3 segments Must have 3 segments

Flow of e-s unidirectionally Flow of e-s in opposite direction

O
O
Practise Questions
Which resonating structure of nitro ethene is never possible?

A. B.

C. D.
Arrange them in order of stability
Most stable resonating structure is

A. B. C. D.
 Predict the least stable structure

I
O

+ II
-
O

+ III
-
O

-
IV
+
O
Rate of attack of Electrophile
Rate of attack of electrophile
Rate of attack of electrophile

Usually +R dominates over -I effect of any group for the rate of

attack of electrophile as well as the site of attack

Except for HALOGENS

For rate of attack, +I >+R

Rate of attack of electrophile
Activating & Deactivating groups
Types of Activating groups
Activating Groups

1. HIGHLY ACTIVATING

1. MODERATELY ACTIVATING

1. WEAKLY ACTIVATING
Types of Deactivating groups
Deactivating Groups

1. HIGHLY DEACTIVATING

1. MODERATELY DEACTIVATING

1. WEAKLY DEACTIVATING
Important note
Note

These can show both +R and -R

H2C = CH -

HN = N-
Practise Questions
In which compounds lone pair is in Resource/delocalised.

NH2
A. E. NH

NH2
B. F. NH

NH2
C. G.
O
NH
D. H.
NH2
Find out localised lone pair sites

N
A. 2

N B. 3
C. 4
N N D. 5

NH2
Compare the compounds for stability

+
X = Number of 𝛑 electrons present in the compound ‘P’
Y = number of 𝛑 electrons involved in conjugation in compound ‘P’
then value of (X-Y) is
In which of the following compound bond order is 1.5 for indicated bond?

A. B.

c. D.
Can O donate to one double bond and take electrons from other
double bond?

Ö
..
Arrange in the order of electrophilic attack
Arrange in the order of electrophilic attack

NH2 O
CH3
Arrange in the order of electrophilic attack

OH O - COCH3
A.

B.

C.
[Jan. 09, 2020 (II)]
D.
Hyperconjugation
Hyper Conjugation
The permanent shifting of π-electron density due to the σ - p
overlapping of CH bond of an alkyl group with conjugated system
Hyper Conjugation
1. Permanent Effect
2. Distance independent effect
3. Stronger than inductive effect
4. Weaker than resonance effect (usually)
 Hyper Conjugation

+H effect is E donating effect and increases e - density at

ortho and para

+H effect depends on strength of C H Bond

No bond resonance / Baker Nathan effect

 Number of Hyperconjugative structures

Total number of H. structure -

= HS not involving CH Bond with p - orbital + HS involving

C - H Bond with p - orbital

= (1 + no. of α H)
Hyperconjugation in ethyl carbocation
Hyperconjugation in propene
Practise Questions
Compounds / Ions which can show hyperconjugation

(i) CH3+ CH2 = CH2

(ii) CH3 - CH•2 CH3 - CH = O

(iii) CH2 = CH2 CH3 - C = O

|
CH3
(iv) CH3 - CH = CH2

(v) CH3 - C ≡ CH
Compare the stability of isomeric alkenes
Calculate the number of Hyperconjugative structures
Arrange the following according to Hyperconjugation when
attached to benzene ring.
A.
B.
C.
D. [Adv. 2013]
[2011]
Aromaticity and Huckel’s rule
 Aromaticity -
Aromatic Compounds :-
All cyclic compounds which are unusually stabilized than its
analogous open chain compound
Rules for compound to be aromatic

Compound must:
A. Be planar : either sp or sp2
B. Be cyclic
C. Conjugated πe-
D. LARGEST CONJUGATED BOUNDARY
(4n + 2) π e-, where n≥0
Anti-Aromatic Compounds

All cyclic compounds which are highly unstable than its open chain
analogous system

Condition for Anti-aromatic compounds:

Compounds must not be

A. Be planar
B. Be cyclic
C. Be conjugated
LARGEST CONJUGATED BOUNDARY

A. Must have 4n π e-
 Note

(i) Anti - aromatic compounds are highly unstable and do not exist at
room temperature.
Non-Aromatic Compounds

All cyclic compounds which are comparatively stable than their

open chain analogous system

Condition for non-aromatic compounds:

Compounds must not be
A. Aromatic
B. Non-Aromatic
Non-Aromatic Compounds
Practise Questions
Find whether the compounds are aromatic/anti aromatic/ non
aromatic
Find whether the compounds are aromatic/anti aromatic/ non
aromatic
Find whether the compounds are aromatic/anti aromatic/ non
aromatic
Find whether the compounds are aromatic/anti aromatic/ non
aromatic
Find whether the compounds are aromatic/anti aromatic/ non
aromatic
Find whether the compounds are aromatic/anti aromatic/ non
aromatic
A. B.

C. [2012]
D.
Stability of Intermediates
 Stability of intermediates : -
Stability of CARBOCATIONS :- EDG (+R > +H > +I)

Stability of RADICALS :- EDG (+R > +I > +H)

Stability of CARBOANION :- EWG (-R > -H > -I)

Practice Questions
Arrange the following in the order of stability.
Arrange the following in the order of stability.
Arrange the following in the order of stability.
 [2013]

A.
B.
C.
D.
Arrange the following in the order of stability.
Arrange the following in the order of stability.
Arrange the following in the order of stability.
Arrange the following in the order of stability.
Dipole Moment
Prediction of dipole moment
Prediction of dipole moment
Practise Questions
A. B.

[April. 09, 2013]

C. D.
A. [Jan. 07, 2020 (II)]
B.
C.
D.
 [2014]

A.
B.
C.
D.
Heat of Combustion
Heat of Combustion
Enthalpy change when one mole of compound is completely burnt
(Oxidation).

HOC ∝ number of C atoms

∝ 1/stability
∝ strain ∝ (HOC/CH2)
Compare the following wrt heat of combustion
Compare the following wrt heat of combustion
Compare the following wrt heat of combustion
Compare the following wrt heat of combustion
A. B.

C.
[Jan. 09, 2020 (I)]

A.
B.
C.
D.
Sigma Resonance/Dancing Resonance
 Sigma Resonance
For cyclopropyl methyl carbocation
Compare the stability of the following
Telegram Channel

tinyurl.com/SAKSHIVORA
 11th / 9, 10

12th / Drop

SAKSHI SAKSHI
 Unacademy
Subscription

LIVE Class Environment Performance Analysis

LIVE Polls & Leaderboard Weekly Test Series
LIVE Doubt Solving DPPs & Quizzes
LIVE Interaction
 India’s BEST Educators Unacademy Subscription

If you want to be the BEST

“Learn” from the BEST
Bratin Mondal Top Amaiya singhal
100 %ile 100 %ile
Results
 11th / 9, 10

12th / Drop

SAKSHI SAKSHI
 Personal Guidance Study Planner
Get one on one guidance Customized study plan
from top exam experts with bi-weekly reviews

Live Classes Weekly Tests

ICONIC PLUS
Structured Unlimited
Courses Access
Test Analysis Study Material
Get one on one guidance Specialised Notes & Practice
from top exam experts Sets

Experts' Guidelines
Study booster workshops by
exam experts
SAKSHI